1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58545553, compound

HRID 417684Notes

Reaction equation

HRID 417684 reaction equation
[S:1]1[C:5]([C:6](O)=[O:7])=[CH:4][CH:3]2[S:9][CH:10]=[CH:11][CH:2]12.C1C=C[C:15]2[N:20]([OH:21])N=NC=2C=1.[CH3:22]CN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[CH3:22][O:21][N:20]([CH3:15])[C:6]([C:5]1[S:1][CH:2]2[CH:11]=[CH:10][S:9][CH:3]2[CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 600973103a,6a-Dihydrothieno[3,2-b]thiophene-2-carboxylic acid

Product 1

HCID 58545553HCID 58545553, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3a,6a-Dihydro-thieno[3,2-b]thiophene-2-carboxylic acid (2 g, 10.86 mmol) MeNHOMe—HCl (1.06 g, 10.86 mmol), HOBt (1.47 g, 10.86 mmol) and DIPEA (5.9 mL, 33.67 mmol) were combined in DMF (40 mL). To the stirred mixture was added EDCI (2.72 g, 14.12 mmol). After 5 h, EtOAc (100 mL) was added and the organics were washed with saturated aqueous NaHCO3 and brine then dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (20% to 45% EtOAc/Hex) to afford the title compound (1.98 g, 80%).

Workup

  1. washthe organics were washed with saturated aqueous NaHCO3 and brine
  2. dry with materialthen dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica column chromatography (20% to 45% EtOAc/Hex)

Sources & evidence

ORD record
ord-44f26e9690994ec2a6dbbef26d0737e9
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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